Before 2023, I prayed the way most busy founders pray. Quickly. Transactionally. A request filed before a meeting the way you might check your phone for the weather.
Then I had a lot of time that I could not fill with meetings.
What changes when you cannot leave
The first thing you notice, when the calendar is gone, is how much of what you called thinking was actually just scheduling. The mind, deprived of its forward motion, does something unexpected: it stops solving and starts receiving.
I had read enough theology to know the word contemplation. I had never had enough silence to practice it. Inside, I had nothing but silence, and it turned out that silence is not nothing. It is a substance. It has texture. And most of what I had been trying to avoid with noise turned out to be worth sitting with.
The men in the cell
There was a young man who had grown up in a state orphanage. His faith, if you could call it that, was raw and without category. He did not pray with words. He sat very still in the morning and seemed to be doing something interior that I recognized but could not name.
I asked him once what he was doing. He said he was listening.
That word rearranged something in me. Not speaking. Not asking. Listening. To what, I pressed. To whatever wants to come in, he said.
He had no theological training. He had arrived at contemplative prayer through thirty years of surviving without anyone to ask for help.
The transaction problem
Most prayer, as I practiced it, was transactional. God, help this deal close. God, protect my family. God, let this regulation pass. These are not bad prayers. But they share a structural assumption: that prayer is a mechanism for influencing outcomes.
What I found inside was that prayer can be something else. Not a request but an orientation. Not a conversation with someone who controls what happens, but a way of attending — to what is present, what is true, what is actually being asked of you in this moment.
The distinction matters practically. Transactional prayer produces a kind of low-grade anxiety when outcomes do not match requests. Contemplative prayer — if I can use that word without making it too complicated — produces something closer to what the New Testament calls peace that passes understanding. Not the absence of difficulty. Presence in it.
What I brought back
I still pray before meetings. I wrote about that before. But I pray differently now.
Before, I was praying for the meeting to go well. Now I am more often asking to be present to what is actually happening in the room — what the other person needs, what is being left unsaid, what the right move is that I cannot yet see.
The difference in outcomes is not dramatic. But the difference in who I am in the room is.
I learned this from a man with no education, in a place neither of us chose, through a practice he invented because he had nothing else.
That is not the theology I was trained in. It is the one that has held.